View More View Less
  • 1 University of Belgrade, Vojvode Stepe 450, Belgrade, Serbia
Restricted access

The retention behavior and lipophilicity of aripiprazole and its nine impurities as well as ziprasidone and its five impurities have been examined by thin-layer chromatography using RP-18 stationary phase and different mixtures of methanol, water, and ammonia; and ethanol, water, and ammonia as the mobile phases. In both examined chromatographic systems, linear relationships were established between retention parameters and the volume fraction of the methanol and ethanol in mobile phase (r > 0.948 for methanol and r > 0.971 for ethanol). Correlation matrices obtained between experimentally obtained lipophilicity indices (RM0, m, and C0) and calculated log P values showed that, for the examined antipsychotics and their impurities, RM0 and m values are more reliable lipophilicity parameters compared to C0 values. In addition, the performed principal component analysis (PCA) has provided new information about the similarity and differences between the tested compounds as well as the experimental lipophilicity indices and calculated log P values. The experimentally obtained RM0 values and the computed molecular parameters of the examined compounds were further used for the quantitative structure—retention relationship (QSRR) study in order to determine the most important properties governing retention. The QSRR modeling was performed by use of the partial least squares regression, and predictive performances of the developed QSRR models were tested by use of the cross-validation and external test set prediction. The obtained results revealed that, apart from lipophilicity, topological descriptors and molecular weights of the tested compounds have the strongest influence on the retention behavior of the examined antipsychotics and their impurities in reversed-phase thin-layer chromatography. The predictive performance of the developed QSRR model suggests its applicability for a reliable prediction of the retention behavior of the congeners.

  • [1]

    T.L. Lemke , D.A. Williams, V.F. Roche, S.W. Zito, Foye’s Principles of Medicinal Chemistry, 7th edn., Lippincott Williams & Wilkins, Baltimore, MD, 2012, 449484.

    • Search Google Scholar
    • Export Citation
  • [2]

    W.M. Greenberg , L. Citrome, CNS Drug Rev. 13 (2007) 137177.

  • [3]

    B.G. Katzung , Basic & Clinical Pharmacology, Antipsyhotic Agents & Litium, Lange Medical Books/McGraw-Hill, San Francisco, CA, 2004.

  • [4]

    European Pharmacopoeia, 9th edn., Council of Europe, Strasbourg, 2014.

  • [5]

    United States Pharmacopoeia, 38NF-33, US Pharmacopeia Convention, Rockville, MD, 2015.

  • [6]

    K. Nikolic , M. Pavlovic, A. Smoliński, D. Agbaba, Comb. Chem. High T. Scr. 15 (2012) 730744.

  • [7]

    K. Nikolic , N. Djordjević Filijović, B. Maričić, D. Agbaba, J. Sep. Sci. 36 (2013) 31653175.

  • [8]

    D. Obradovic , S. Filipic, K. Nikolic, D. Agbaba, J. Planar Chromatogr. 29 (2016) 239246.

  • [9]

    K.S.V. Srinivas , R. Buchireddy, G. Madhusudhan, K. Mukkanti, P. Srinivasulu, Chromatographia 68 (2008) 635640.

  • [10]

    N.R. Pai , D.S. Dubhashi, Pharm. Lett. 2 (2010) 110.

  • [11]

    G.V.R. Reddy , A.P. Kumar, B.V. Reddy, P. Kumar, H.D. Gauttam, Eur. J. Chem. 1 (2010) 2027.

  • [12]

    A. Singh , B.M. Rao, G.R. Desphie, S. Sangaraju, M.K. Srinivasu, M.L. Devi, P.V.V. Satyanarayana, K.B. Chirasekhar, Chromatographia 65 (2007) 191196.

    • Search Google Scholar
    • Export Citation
  • [13]

    Z.A. El-Sherif , B. El-Zeany, O.M. El-Houssini, M.S. Rashed, H.Y. Aboul-Enein, Biomed. Chromatogr. 18 (2004) 143149.

  • [14]

    D. Zakowiecki , K. Cal, Acta Pol. Pharm. 69 (2012) 809819.

  • [15]

    S. Ray , S.K. Kumari, C. Krishnaiah, N.A. Rao, J. Liq. Chromatogr. Relat. Technol. 36 (2013) 968982.

  • [16]

    I. Mohamed , W.F. Belal, N. El-Enany, M. Eid, R.N. El-Shaheny, J. Fluoresc. 21 (2011) 16591667.

  • [17]

    N. Djordjevic-Filijovic , A. Pavlovic, K. Nikolic, D. Agbaba, Acta Chromatogr. 26 (2014) 1328.

  • [18]

    M. Pavlovic , M. Malesevic, K. Nikolic, D. Agbaba, J. AOAC Int. 94 (2011) 713722.

  • [19]

    D. Obradovic , S. Filipic, K. Nikolic, M. Carapic, D. Agbaba, J. Liq. Chromatogr. Relat. Technol. 39 (2016) 271276.

  • [20]

    K. Ciura , A. Rutecka, P. Kawczak, J. Nowakowska, J. Planar Chromatogr. 30 (2017) 225230.

  • [21]

    R. Skibiński , G. Misztal, Ł. Komsta, A Korólczyk, J. Planar Chromatogr. 29 (2006) 7380.

  • [22]

    R. Skibiński , Ł. Komsta, G. Misztal, J. Planar Chromatogr. 20 (2007) 7580.

  • [23]

    J. Veličković , D. Andrić, G. Roglić, Ž. Tešić, D. Milojković-Opsenica, J. Planar Chromatogr. 17 (2004) 255260.

  • [24]

    E.C. Bate-Smith , R.G. Westall, Biochim. Biophys. Acta 4 (1950) 427440.

  • [25]

    E. Soczewiński , C.A. Wachtmeister, J. Chromatogr. 7 (1962) 311320.

  • [26]

    M.L. Bieganowska , A.D. Szopa, A. Petruczynik, J. Planar Chromatogr. 8 (1995) 122128.

  • [27]

    A. Pyka , M. Miszczyk, Chromatographia 61 (2005) 3742.

  • [28]

    ChemAxonMarvin 6.1.0, Budapest, Hungary, 2013, http://www.chemaxon.com

  • [29]

    CambridgeSoft Corporation, ChemBio3D Ultra, Version 13.0. Cambridge, MA, 2013.

  • [30]

    J.J.P. Stewart , J. Comput. Chem. 10 (1989) 209220.

  • [31]

    J.J.P. Stewart , J. Comput. Chem. 10 (1989) 221264.

  • [32]

    C.C.J. Roothan , Rev. Mod. Phys. 23 (1951) 6989.

  • [33]

    Dragon 6, TALETE srl, Via V. Pisani, 13, 20124 Milano, Italy, 2010, http://www.talete.mi.it

  • [34]

    VCCLAB, Virtual Computational Chemistry Laboratory, 2005, http://www.vcclab.org

  • [35]

    Molinspiration Cheminformatics, Nova ulica, SK-900 26 Slovensky Grob, Slovak Republic, 2006, http://www.molinspiration.com/

  • [36]

    Chem3D Ultra7.0, Cambridge Soft Corporation,100 Cambridge Park Dr, Cambridge, USA, 2001, http://www.cambridgesoft.com

  • [37]

    ACD/I-Lab, Advanced Chemistry Development, Inc., Toronto, ON, Canada, 2015, http://www.acdlabs.com/resources/ilab/

  • [38]

    Umetrics AB, SIMCA P+ program, Version 12.0.0.0, Umeå, May 20, 2008, www.umetrics.com.

  • [39]

    S. Filipic , D. Ruzic, J. Vucicevic, K. Nikolic, D. Agbaba, J. Pharmaceut. Biomed. Anal. 127 (2016) 101111.

  • [40]

    S. Wold , E. Johansson, M. Cocchi, in: H. Kubinyi (ed.), 3D QSAR in Drug Design, Theory, Methods, and Applications, ESCOM Science Publishers, Leiden, 1993, pp. 523550.

    • Search Google Scholar
    • Export Citation
  • [41]

    J.G. Topliss , R.P. Edwards, J. Med Chem. 22 (1979) 12381244.

  • [42]

    L. Eriksson , E. Johansson, N. Kettaneh-Wold, J. Trygg, C. Wikstrom, S. Wol (eds.), Multi- and M egavariate Data Analysis. Basic Principles and Applications I, 2nd edn., Umetrics Academy, Umeå, 2001.

    • Search Google Scholar
    • Export Citation
  • [43]

    P.K. Ojha , K. Roy, Chemometr. Intell. Lab. 109 (2011) 146161.

  • [44]

    K. Roy , K. Supratik, A. Pravin, Chemometr. Intell. Lab. 145 (2015) 2229.

  • [45]

    P.K. Ojha , I. Mitra, R.N. Das, K. Roy, Chemometr. Intell. Lab. 107 (2011) 194205.

  • [46]

    S. Filipic , A. Antic, M. Vujovic, K. Nikolic, D. Agbaba, J. Chromatogr. Sci. 54 (2016) 11371145.

  • [47]

    R. Mannhold , G.I. Poda, I.V. Tetko, J. Pharm. Sci. 98 (2009) 861893.

For Submission Guideline click HERE

Manuscript Submission: JPC Manuscript Submission

  • Impact Factor (2019): 0.815
  • Scimago Journal Rank (2019): 0.322
  • SJR Hirsch-Index (2019): 30
  • SJR Quartile Score (2019): Q3 Analytical Chemistry
  • SJR Quartile Score (2019): Q3 Clinical Biochemistry
  • SJR Quartile Score (2019): Q4 Biochemistry
  • Impact Factor (2018): 0.826
  • Scimago Journal Rank (2018): 0.291
  • SJR Hirsch-Index (2018): 29
  • SJR Quartile Score (2018): Q3 Analytical Chemistry
  • SJR Quartile Score (2018): Q4 Clinical Biochemistry

Language: English

Founded in 1988
Publication: One volume of six issues annually
Publication Programme: 2020. Vol. 33.
Indexing and Abstracting Services:

  • Science Citation Index
  • Sci Search Research Alert
  • Chemistry Citation Index and Current Content/Physical
  • Chemical and Earth Sciences

Senior editors

Editor(s)-in-Chief: B. Spangenberg

Managing Editor: Kakuk Ágnes

Editorial Board

  • T.H. Dzido (Lublin, Poland)
  • Á. M. Móricz (Budapest, Hungary)
  • C.F. Poole (Detroit, MI, USA)
  • E. Reich (Muttenz, Switzerland)
  • B. Renger (Radolfzell, Germany)
  • I. Vovk (Ljubljana, Slovenia)

 

Advisory Board

  • E. BODOKI (Cluj-Napoca, Romania)
  • U. A. TH. BRINKMAN (Amsterdam, The Netherlands)
  • I. CHOMA (Lublin, Poland)
  • V. COMAN (Cluj-Napoca, Romania)
  • W. DAMMERTZ (Kressbronn, Germany)
  • K. FERENCZI-FODOR (Budapest, Hungary)
  • G. INDRAYANTO (Surabaya, Indonesia)
  • R. E. KAISER (Bad Dürkheim, Germany)
  • I. KLEBOVICH (Budapest, Hungary)
  • T. KOWALSKA (Katowice, Poland)
  • L. LEPRI (Florence, Italy)
  • E. MINCSOVICS (Budapest, Hungary)
  • D. NUROK (Indianapolis, IN, USA)
  • B. RENGER (Radolfzell, Germany)
  • J. K. RÓŻYŁO (Lublin, Poland)
  • J. SHERMA (Easton, PA, USA)
  • M. WAKSMUNDZKA-HAJNOS (Lublin, Poland)
  • D. WEDGE (Mississippi, USA)

A. Kakuk - Managing Editor, Akadémiai Kiadó
Address: P.O. Box 245. H-1519 Budapest, Hungary
Fax: +36 1 464 82 95
E-mail: jpc@akkrt.hu